4-ethynyl-2-fluorobenzonitrile

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4-ethynyl-2-fluoro-benzonitrile (1.29 g, 8.9 mmol) in EtOAc (30 mL) was placed in a Parr pressure bottle and palladium on carbon (130 mg of 10% on carbon) was added. The bottle was placed on the Parr hydrogenation apparatus and shaken under 10 psi of hydrogen pressure. After shaking for two hours the black suspension was filtered through a pad of Celite. The pad was washed thoroughly with EtOAc, and the combined filtrates were concentrated under reduced pressure. The residue was taken up in toluene and concentrated under reduced pressure to afford 4-ethyl-2-fluoro-benzonitrile (1.19 g, 89% yield). 1H-NMR (400 MHz, CDCl3): δ 7.55-7.50 (1H, m), 7.11-7.03 (2H, m), 2.72 (2H, q, J=7.6 Hz), 1.26 (3H, t, J=7.6 Hz). was added was filtered through a pad of Celite The pad was washed thoroughly with EtOAc the combined filtrates were concentrated under reduced pressure concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4-ethynyl-2-fluoro-benzonitrile (1.29 g, 8.9 mmol) in EtOAc (30 mL) was placed in a Parr pressure bottle and palladium on carbon (130 mg of 10% on carbon) was added. The bottle was placed on the Parr hydrogenation apparatus and shaken under 10 psi of hydrogen pressure. After shaking for two hours the black suspension was filtered through a pad of Celite. The pad was washed thoroughly with EtOAc, and the combined filtrates were concentrated under reduced pressure. The residue was taken up in toluene and concentrated under reduced pressure to afford 4-ethyl-2-fluoro-benzonitrile (1.19 g, 89% yield). 1H-NMR (400 MHz, CDCl3): δ 7.55-7.50 (1H, m), 7.11-7.03 (2H, m), 2.72 (2H, q, J=7.6 Hz), 1.26 (3H, t, J=7.6 Hz). was added was filtered through a pad of Celite The pad was washed thoroughly with EtOAc the combined filtrates were concentrated under reduced pressure concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2-fluoro-4-(3-hydroxy-3-methyl-but-1-ynyl)-benzonitrile (2.6 g, 13 mmol) in toluene (55 mL) was added NaH (53 mg of a 60% suspension in mineral oil, 1.3 mmol). The reaction mixture was heated to reflux. After refluxing for several hours, heating was discontinued, and the cooled reaction mixture was quenched by the addition of 2M Na2CO3 solution. The layers were separated and the toluene layer was washed with H2O (2×20 mL), brine (25 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product. The crude material was purified by flash chromatography eluting with a gradient from 0% to 10% ethyl acetate/hexane to afford 4-ethynyl-2-fluoro-benzonitrile (1.25 g, 66% yield). 1H-NMR (400 MHz, CDCl3): δ 7.61-7.57 (1H, m), 7.38-7.30 (2H, m), 3.36 (1H, s). The reaction mixture was heated to reflux After refluxing for several hours heating the cooled reaction mixture was quenched by the addition of 2M Na2CO3 solution The layers were separated the toluene layer was washed with H2O (2×20 mL), brine (25 mL) dried over Na2SO4 filtered concentrated under reduced pressure to afford the crude product The crude material was purified by flash chromatography eluting with a gradient from 0% to 10% ethyl acetate/hexane

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4-ethynyl-2-fluoro-benzonitrile (1.29 g, 8.9 mmol) in EtOAc (30 mL) was placed in a Parr pressure bottle and palladium on carbon (130 mg of 10% on carbon) was added. The bottle was placed on the Parr hydrogenation apparatus and shaken under 10 psi of hydrogen pressure. After shaking for two hours the black suspension was filtered through a pad of Celite. The pad was washed thoroughly with EtOAc, and the combined filtrates were concentrated under reduced pressure. The residue was taken up in toluene and concentrated under reduced pressure to afford 4-ethyl-2-fluoro-benzonitrile (1.19 g, 89% yield). 1H-NMR (400 MHz, CDCl3): δ 7.55-7.50 (1H, m), 7.11-7.03 (2H, m), 2.72 (2H, q, J=7.6 Hz), 1.26 (3H, t, J=7.6 Hz). was added was filtered through a pad of Celite The pad was washed thoroughly with EtOAc the combined filtrates were concentrated under reduced pressure concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2-fluoro-4-(3-hydroxy-3-methyl-but-1-ynyl)-benzonitrile (2.6 g, 13 mmol) in toluene (55 mL) was added NaH (53 mg of a 60% suspension in mineral oil, 1.3 mmol). The reaction mixture was heated to reflux. After refluxing for several hours, heating was discontinued, and the cooled reaction mixture was quenched by the addition of 2M Na2CO3 solution. The layers were separated and the toluene layer was washed with H2O (2×20 mL), brine (25 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product. The crude material was purified by flash chromatography eluting with a gradient from 0% to 10% ethyl acetate/hexane to afford 4-ethynyl-2-fluoro-benzonitrile (1.25 g, 66% yield). 1H-NMR (400 MHz, CDCl3): δ 7.61-7.57 (1H, m), 7.38-7.30 (2H, m), 3.36 (1H, s). The reaction mixture was heated to reflux After refluxing for several hours heating the cooled reaction mixture was quenched by the addition of 2M Na2CO3 solution The layers were separated the toluene layer was washed with H2O (2×20 mL), brine (25 mL) dried over Na2SO4 filtered concentrated under reduced pressure to afford the crude product The crude material was purified by flash chromatography eluting with a gradient from 0% to 10% ethyl acetate/hexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4-ethynyl-2-fluoro-benzonitrile (1.29 g, 8.9 mmol) in EtOAc (30 mL) was placed in a Parr pressure bottle and palladium on carbon (130 mg of 10% on carbon) was added. The bottle was placed on the Parr hydrogenation apparatus and shaken under 10 psi of hydrogen pressure. After shaking for two hours the black suspension was filtered through a pad of Celite. The pad was washed thoroughly with EtOAc, and the combined filtrates were concentrated under reduced pressure. The residue was taken up in toluene and concentrated under reduced pressure to afford 4-ethyl-2-fluoro-benzonitrile (1.19 g, 89% yield). 1H-NMR (400 MHz, CDCl3): δ 7.55-7.50 (1H, m), 7.11-7.03 (2H, m), 2.72 (2H, q, J=7.6 Hz), 1.26 (3H, t, J=7.6 Hz). was added was filtered through a pad of Celite The pad was washed thoroughly with EtOAc the combined filtrates were concentrated under reduced pressure concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2-fluoro-4-(3-hydroxy-3-methyl-but-1-ynyl)-benzonitrile (2.6 g, 13 mmol) in toluene (55 mL) was added NaH (53 mg of a 60% suspension in mineral oil, 1.3 mmol). The reaction mixture was heated to reflux. After refluxing for several hours, heating was discontinued, and the cooled reaction mixture was quenched by the addition of 2M Na2CO3 solution. The layers were separated and the toluene layer was washed with H2O (2×20 mL), brine (25 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product. The crude material was purified by flash chromatography eluting with a gradient from 0% to 10% ethyl acetate/hexane to afford 4-ethynyl-2-fluoro-benzonitrile (1.25 g, 66% yield). 1H-NMR (400 MHz, CDCl3): δ 7.61-7.57 (1H, m), 7.38-7.30 (2H, m), 3.36 (1H, s). The reaction mixture was heated to reflux After refluxing for several hours heating the cooled reaction mixture was quenched by the addition of 2M Na2CO3 solution The layers were separated the toluene layer was washed with H2O (2×20 mL), brine (25 mL) dried over Na2SO4 filtered concentrated under reduced pressure to afford the crude product The crude material was purified by flash chromatography eluting with a gradient from 0% to 10% ethyl acetate/hexane